Seriously Funny

Seriously Funny

When a health scare with his infant son thrust him into the red-hot center of the health-care debate last spring, Jimmy Kimmel stepped into the previously no-personal-politics zone of his show and articulated a position that wasn't exactly liberal or conservative so much as sensible and decent. In doing so, he's emerged as something like the most sane and rational voice in an increasingly insane and irrational America.

Jimmy Kimmel doesn’t want to cry. Not tonight, in front of millions. This is something he really, really, really would like to avoid. Jesus.

On this December Monday, as the clock ticks closer to showtime, he can already envision it: Out he’ll come, in a perfectly fitted dark suit and a light blue tie, to amped-up applause, cymbals, and flatulent horn flourishes, and everything will putter down to silence, and he’ll be standing there alone and heave a deep breath, and right there in front of a studio audience of 177 previously whooping vacationers, his eyes might start tearing up and, in place of a joke, he’ll have to say something about Billy, his 7-month-old son, who just went for his second surgery on a faulty heart, because Jimmy had to take the week off, and he and his wife, Molly, who is also a head writer on the show, traded off nights at the hospital not sleeping, and CNN reported the results, which were good—the operation was a success!—and Billy went from panting a lot to suddenly having a bunch of energy, even if he was a little constipated. And because America cares, and because his in-box got flooded yet again beyond the normal 300 e-mails a day, Jimmy, the father, and Jimmy Kimmel, the entertainer, both-of-them-at-once are going to have to say something, and he already knows what he wants to say, that’s the easy part—he always knows what he wants to say. It’s the emotional part he can’t trust.

There’s been a lot of deep sighing while he’s been sitting at the computer, writing his monologue today. In it, he wants to make a point: that our government has failed to extend funding for the Children’s Health Insurance Program (CHIP), which protects one in eight kids in this country who need coverage for catastrophic care of some sort. The fact is that an otherwise bipartisan piece of legislation that protects sick kids has been turned into what Jimmy calls a “bargaining chip” in Congress, and it makes him mad.

When Jimmy returned to the show last spring after Billy had his first heart surgery, at birth, he used his monologue to talk about all those other kids in the hospital, and all those parents, going through their own miseries, and all those caring doctors, and our crummy government trying to take health care from millions of people, and he just couldn’t help getting emotional. The tears came again when his uncle Frank died, and Don Rickles died, because he so loved them. The tears came, too, right as he opened his mouth—he couldn’t help himself—after the mass shooting in Las Vegas, his hometown, with 59 dead, because he was angry and destroyed like the rest of us, saying that “it’s the kind of thing that, it makes you want to throw up or give up.… It feels like someone has opened a window into hell.”

That one was, in some ways, the Gettysburg Address of late-night monologues, now viewed nearly 10 million times on YouTube, having become a lightning rod. As politicians offered empty condolences and prayers, Jimmy Kimmel was the one who talked common sense to us, and protested, and asked for us to protest with him, who seemed the only Voice of Reason occupying any sort of pulpit. It was as real as realness gets. Like the screen split open and the late-night talk-show host became your neighbor at the door, in distress. It was this guy Jimmy saying, Enough is enough, this is madness. Please.

Of course, he’s taken some heat for the tears. Howard Stern, one of his closest friends, razzed him on his radio show with a song called “Jimmy Kimmel Cries,” featuring samples of Jimmy blubbering on-air. In another case, a so-called guerrilla artist put up posters around Los Angeles, including on the backs of bus-stop waiting benches, mocking him, calling his show The Jimmy Kimmel Estrogen Hour. (Jimmy’s response was to be photographed on one such bench, flipping the bird.) And the testy right, seeing how powerful he’s become in the debates over gun control and health care, would like America to see him as a lightweight liberal-elite crybaby.

But still—the shows of emotion have given him an authenticity that the other late-night hosts just don’t have.

“I know, I know,” he says. “I understand the but. My wife always says, ‘It’s beautiful.’ And yet, I still wish I could keep it together. I see others keeping it together, and it makes me wonder if I’m emotionally unstable. My dad is the same way. He’s definitely the same way. We don’t express a great deal of emotion, but when we do, it really comes pouring out.”

“I’ve been the exact same guy since I was 20 years old. I haven’t changed at all, really. For somebody who does nothing but fuck around, I don’t fuck around.”

This Monday in December, though, he has an idea. The idea is to bring Billy out in his arms at the top of the show. It seems right to have Billy there after what they’ve been through, and to share him with the world, and to talk about health care. Billy’s wearing an outfit that Kim and James Taylor sent as a baby gift, and the odds are Billy will start crying, and Jimmy will be so busy doing the comforting that he won’t have time to cry himself. This could really work.

Mid-afternoon, Molly arrives with the kids: curly-haired Jane, who is 3, and Billy. It’s a family day at the show. Downstairs, Santa Claus and the Chanucorn—a made-up Chanukah unicorn with a menorah for a horn that has starred on the show before—are taking wishes and handing out candy.

“I’m really afraid Billy’s going to cry,” says Molly.

“We gotta get a hand-off plan,” says Jimmy. “Maybe we give him a zwieback.”

“But it can’t get mushy,” says Molly. Jimmy and Molly, being comedians, will say anything to each other—anything at all—to get a laugh. But now Jimmy looks serious, like he has something really serious to say after the week they just had. “When you come out, I want you dressed like a whore,” says Jimmy, and Molly bursts out laughing.

“Wouldn’t that be great?” she says. “All whorish! See you later!” And then she’s gone, off with the kids so Jimmy can go back to his computer, to the flood of jokes and fact-checks he must sift through as go-time approaches.

At five minutes before five, the writers assemble in Jimmy’s office. They’ve been doing this for 15 years now—from the awkward first days of the show when they went on live and it might have been a little too loose to the juggernaut they’ve become—a group chant before Jimmy goes out. A little slip of paper gets handed to everyone but Jimmy. They like to surprise him.

“BILLY SAYS HE WON’T CRY IF YOU PROMISE NOT TO, EITHER!” they yell in unison. “BEST SHOW EVER!”

And minutes later, there’s Jimmy, appearing before the cheering audience, holding Billy. Billy is wide-eyed, ogling the crowd, cradled in his father’s arms in his James Taylor outfit, seemingly the most even-keeled kid you’ve ever seen in the bright lights.

“I was out last week because this guy had heart surgery,” says Jimmy, his voice catching a little, “but, look, he’s fine, everybody! He may have pooped, but he’s fine!” Laughter. He thanks the guest hosts who filled in during his absence, looks down at Billy again, and seems to enter a wordless freeze looking at him, which of course is when he tears up.

It’s rare on network TV to have a second of absolute silence, no bells or whistles, buzzers or boings. And Jimmy: It’s not a gusher, but a surge of emotion, a father and baby son on national TV, in a real moment. By bringing him out here, by discussing the failure of Congress to pass CHIP and posting a number for people to call, Jimmy the father speaks through Jimmy Kimmel the entertainer: This matters. This really, really fucking matters.

And then he delivers the laugh line of the night: “Daddy cries on TV, but Billy doesn’t! It’s unbelievable.”

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Jimmy Kimmel has a place in the South Bay where he spends weekends. He bought it more than ten years ago, nothing overly fancy, set back a couple blocks from the water. If you passed it, you’d never suspect Jimmy Kimmel lives there, with its garage full of kid stuff, just another house in the row. Over lunch at an “old people’s joint” nearby, he’s telling me something that would surprise most people.

“I’ve been the same exact guy since I was 20 years old,” he says. When he’s not on TV—they tape the show up in Hollywood, near his other house, four nights a week—Jimmy favors jeans and the collared, multi-pocketed short-sleeve shirt you might wear fly-fishing. Because of his role hosting The Man Show in the early aughts, a show meant to lampoon men, people mistook Jimmy Kimmel for the boorish man-child he played, egged on by the frat-boy audience. But in fact he’s been boringly grown-up since college. “I would never join a fraternity,” he says. (And for what it’s worth, he also cried on the last episode of The Man Show.) “I haven’t changed at all, really. I don’t think I’ve been on a casual date before in my life. I have no interest in a superficial relationship. None. I don’t even know if I could get a boner in that situation.”

Instead, he characterizes himself as a workaholic narcoleptic with a dash of OCD tossed in. He’s known for, and exhibits, laser focus, especially sitting at the middle of the maelstrom at work each day, with writers and producers, friends and family, coming and going as he bangs out the monologues and jokes. (While I spent the day on a nearby couch, he never made it ten feet from his computer before he got drawn back in, writing new ideas, re-writing sentences, unable to let anything go until the time came for makeup, in a closet-sized room just outside his office door where he re-read it all while his makeup artist plied her craft on him.) He keeps lists out the wazoo. His Christmas list alone includes hundreds of people he buys for, doling out well over $100,000 on gifts and everything else. His Christmas Eve dinner file includes the menu, with little notes of castigation from each past year, next year get 30 pounds of crab legs, for instance, put the crudo out earlier. He makes the traditional Italian Feast of the Seven Fishes, but with somewhere between 20 and 25 fishes.

His mother claims her son tested as a genius in the delivery room, growing up Catholic in a tight German-Italian-Irish family in Brooklyn’s Mill Basin neighborhood. Little Jimmy was smart, funny, shy, and loyal as hell as a friend. He moved to Las Vegas when he was 9. The first time his boyhood buddy (and now sax-playing bandleader) Cleto Escobedo laid eyes on him, Jimmy was riding his bike down the street, wearing boxing gloves, on his way to beat someone up. “People made fun of my Brooklyn accent,” he says. “I was a little squirt of a kid, but I was quick to fight. I had to calm down and learn the ways of the West Coast.”

His shyness was almost a disability, one he carries to this day. (In fact, an advantage to celebrity, he says, is that people sort of know you, so he doesn’t have to break the ice anymore.) As a teenager, he couldn’t bring himself to accept a sandwich, or even a glass of water, from a friend’s mother. He remembers getting an F on a test while at Arizona State because sitting in a class among hundreds taking the same test, he couldn’t muster the courage to ask someone if he could borrow a pencil, having forgotten his. When he found his first girlfriend, he married her, at 20—he wasn’t legal to drink at his own wedding—and they soon had two kids together, Katie and Kevin. “I thought that’s what you did,” he says. “It didn’t seem unusual to me because my mother was 20 when she had me.”

“I do remember my ex-wife asking me, ‘What’s the plan B if this doesn’t work out?’ And I said, ‘Just to be clear, there is no plan B. There’s plan A, and that’s where the alphabet ends.’ ”

All the while, he was absolutely driven to do what he loved most: make people laugh. Sure, his family was funny, his grandfather in particular, who for no discernible reason once wore a women’s wig to a wedding, acting as if it were his normal hair. But Jimmy’s shtick, his jokes for a wider audience, started in the classroom, and making prank phone calls with friends, and grew from there. “I always knew I could make people laugh,” he says. The pranks grew more elaborate—he called in to the local radio station and did bits. He became a minor high school celebrity, but he wanted more.

“I remember being a little disappointed in myself when I was 17 and I wasn’t famous,” he says. “My definition of famous wasn’t necessarily being on the cover of this magazine. My definition of famous was being a character on a local radio station, because I liked the attention of being a jokester in class.”

After marrying, he got his first paying radio job, in Seattle. And others in Tampa, Palm Springs, Tucson, and eventually in L.A., at the legendary rock station KROQ, where he wrote jokes and did sports. For the most part, he wasn’t climbing the ladder, exactly; he was quailing sideways. “Oh, I was fired many, many times,” he says. “I was not very diplomatic. I rubbed almost every one of my bosses the wrong way. The rest of the staff loved me, but the bosses… In Seattle my partner Kent and I would secretly tape our meetings when our program director was yelling at us, and we’d play them back on the air the next day. And then I genuinely could not understand why he’d be angry about it. I was like, ‘Isn’t this what’s best for the show, what’s best for all of us here?’ I was oblivious. I was not reading other people well.”

It took a long time for him to calibrate, it turns out. The unfettered, uncensored impulse that makes great humor was both the thing he kept chasing and the thing that kept dooming him. The “on” switch was always on, until he got canned and bounced off the air again. Meanwhile, a friend and former intern of his along the way, Carson Daly, hit it big, and then so did another guy he’d befriended, Adam Carolla. He kept waiting, and waiting, for his day, too, all the while juggling young kids and the jobs du jour.

Remembering those days, Jimmy gets a little riled up. In fact, it’s the only time I see a flash of not quite anger but something close: “One of the things that really burns my ass, when people describe me as a member of ‘the Hollywood elite,’ is the 12 years of eating shit and making no money and going to the ATM and hoping that you have more than $20 so that you can eat lunch. That’s the thing that really gets under my skin. Because, you know, I was raised in a middle- to lower-middle-class family, in a very humble neighborhood in Las Vegas, and I am not under the impression that I deserve to make millions of dollars. It just so happens that the job I was fortunate enough to get pays very well. But as far as paying dues goes, I definitely paid them. I had two little kids. I would get fired from job after job, making $20,000 a year, $25,000 a year. I’d have to move across the country. Just the cost of moving would wipe me out.” At the bottom, he moved back in with his parents, interviewing for a job as a car salesman, for which he was rejected. “I think I wasn’t wearing enough cologne,” he jokes.

“I do remember my ex-wife asking me, ‘What’s the Plan B?’ and I said, ‘Just to be very clear, there is no Plan B. There’s Plan A, and that’s where the alphabet ends.’ ”

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Another sunny Los Angeles afternoon, fires burning somewhere in close proximity up the coast, and we’re at the other house now, talking about penises, as all the Christmas loot keeps piling inside the gate.

It’s obviously a bad time for penises, a very bad time, so we’re drinking a whisper of scotch. “The penis has always been dangerous,” says Jimmy. “It’s the most dangerous part of our bodies. The penis makes you do strange things. That said, I would never give mine up.” One of his great heroes—besides David Letterman and Don Rickles—is Howard Stern, with whom he vacations in the Hamptons, and Jimmy says one of the most valuable lessons he learned from Howard was his willingness to be funny, to make himself vulnerable, to sacrifice himself for comedy: “I think Howard was the first person to say he has a small penis. It was so unbelievably outrageous and disarming, you know? For me, it was a light bulb. It’s like, ‘Okay, being funny is more important than being cool,’ I guess. Every guy wants people to think you have a big penis. Not just women, but for some reason your friends, too. It makes no sense at all! For him to just come out and talk about how small his penis is, it had to have been unprecedented. I don’t think Steve Allen was talking about that.”

It reminds Jimmy of being at a party years ago, where a drummer from a very popular ’90s band—who will remain nameless—decided to get completely naked and hang upside down from a rope or something. “He had a very small penis, and I remember being so, almost proud of him, because if he had a big dick and he got naked at a party, I would have thought he was an asshole. But because he had such a small one, I really had nothing but admiration for him.”

When a subject like this comes up, Jimmy seems to hold it in his hand like a piece of fruit, rotating it, checking its luster and bruises for both its humor and its topicality. The more taboo, the more charged, the better. Judge Roy Moore, Donald Trump, the NRA, our U.S. senators. He steps into the fray of the day with a calm smile, but behind the eyes, you can hear the switchblade of a star debater, the mind already having located the flaw that Jimmy efficiently shows us with regular reasonableness. No one’s better at casually, almost dispassionately, disarming someone by simply pointing out their hypocrisy or letting them slide in their own bullshit. And no one’s quite as fearless, either. If the offense is particularly egregious, as was Moore’s alleged penchant for teenage girls—“Target-wise,” says Jimmy, “he’s topped only by Jared from Subway, maybe not even that”—he will double, triple, quadruple down, returning again and again to the scene of the crime.

Though he’s careful not to take cheap shots, he says. “If Donald Trump is clearly joking about something, I feel like it’s the wrong thing to jump on. Even if it was in poor taste or a bad joke, it has to be…maybe that’s just because I’m a comedian. It has to come from that point of view. I think we need to just stay focused on what’s really important. What’s really important is taking care of each other in various ways.”

When he gets a Twitter rise out of a target, his armpits soak with sweat from joy, the feistier the exchange the better: “I live for moments like that. When I got in a Twitter battle with Kanye, I was so happy. My wife makes fun of me. She’s like, ‘You are so happy right now.’ I’m absolutely beaming. I feel very confident in a situation like that.”

Part of Jimmy’s authority is that he himself doesn’t live a louche life. He tries to live a good one. He believes we should love one another. His staff makes fun of him for being an awkward hugger, hugs you could drive a truck through. He admits he never even had the guts to ask someone to the prom. Even his romance with Molly, the origins of which she’s shared publicly, seems to have taken years to unfold. (She says he clinched the deal when he finally invited her over for dinner, having remembered and prepared all her favorite foods at once: crab claws, pizza, gnocchi, a cheeseburger, and a BLT.)

Coat, $4,180 by Prada/ Sweatshirt, $145, jeans, $165, by Polo Ralph Lauren / Boots, $395, by To Boot New York

“I’ll never be afraid of Jimmy making headlines for the wrong reason,” says Erin, his co-executive producer. “He doesn’t want people to know about all the good things he does, but he’s really one of the good ones.”

Which might explain the source of his own freedom in comedy, what allows him to stand comfortably in the most uncomfortable spaces in our culture, nervy, poking, holding the serious and the antic both in hand. As the Oscars approach—what perhaps will be theOscars of our time, as Hollywood confronts a plague of harassment that has given rise to accusations against Harvey Weinstein, Kevin Spacey, James Toback, Brett Ratner, Jeffrey Tambor, et al.—Jimmy, as host, will go wading into the mess once again, in front of more than 30 million worldwide viewers. “I’m surprisingly not nervous,” he says. “I think there are certain groups of people who think I shouldn’t make any jokes about that situation. And there are groups of people who will be mad if I don’t make jokes about that situation. So you just kind of have to figure it out. Whatever I do will be criticized by someone. Like, ‘You didn’t make enough jokes about Harvey Weinstein.’ ”

It’s something that plays out in the show every night, too. “One news article can write that I didn’t say anything about Harvey Weinstein, and then that becomes fact. Wait a minute.… We didn’t have a show that night, so I don’t know how that applies. It’s like I’m protecting someone I don’t even know. I reject that. That is not my job. It’s the same case with a tragedy. Something terrible happens every day. If you mentioned this and you don’t mention that, then you don’t care about these people. You do have to remind people that ultimately it is a comedy show. Even though we may from time to time talk about serious subjects, if people are not laughing at least three nights out of the week, they’re not going to watch it anymore.”

The nature of that laughter really matters to Jimmy. “You take a risk when you make a comment that is dark,” he continues. “In a way, it’s you saying, ‘I trust you. I trust your sense of humor, and I trust that you will not use this against me.’ It’s a little gift, I think. When somebody makes a truly offensive joke to me, I love them a little bit more. If it’s just offensive, it’s no good. But there’s nothing better than when something emotional or serious is going on, maybe it’s a wedding toast, and somebody funny leans over and whispers something terrible into your ear. I live for those moments. I live for being the one who does the whispering.”

And so he has, mixing emotions and punch lines, pointing out the foibles of those in power. As someone who’s always featured his family in the show—his pugnacious aunt Chippy has regular hilarious cameos, his cousin Sal is in charge of pranks, his uncle Frank was a beloved character, his son Kevin does social media—it’s natural that his family concerns have made their way into his monologues. But with the Las Vegas shooting, Jimmy veered into territory that even he wasn’t quite ready for, unwittingly positioning himself at the center of a deadly serious debate, and in so doing, made himself a target for weird right-wing threats. Someone called an old interior decorator of his, trying to dig up dirt. There were a lot of unhinged tweets—calling him a “fucking lib-tard,” etc.—but only one possibly credible death threat.

“You might want to turn your tape recorder on for this one,” he says, already tickled. There’s apparently a guy who dresses as Batman for tourist photos, in front of the studio on Hollywood Boulevard, who Jimmy had to ban from the studio for using a racial slur. “So, the Incredible Hulk came to our office and told one of our producers that the guy who dressed as Batman had bought a gun to shoot me. Our crack security team posted pictures of the guy, but in his Batman costume. I don’t think he knew the Hulk ratted him out, so he showed up on the boulevard, and the cops arrested him and took him to jail.”

Suddenly, the stakes are high, so high even Batman’s after him. “Because here’s the thing about it,” says Jimmy. “The late-night talk show has turned into a court of sorts.” In these insane times, we, the powerless, go there to work out our complicated feelings about any given moment, to figure out how to feel about our lack of hope. “Nowadays, we have to pick a side, I guess. People now demand that you lead a public flogging. And if you do it for some and you don’t do it for others, you’re wrong.”

We come for clarity, or at least for a chance to laugh it out at 11:35 P.M. Which is its own sort of power. Still, it’s a lot to ask of our late-night host. Especially from a guy who describes his most dreaded interview question as “anything with the words ‘late-night landscape’ in it.” But such is the new reality. Viewers arrive each night for saving, to have their equilibrium restored, to acquire verbal revenge.

Forget the two houses, at the beach, in the hills: That moment each night at the top of the show, that’s where Jimmy Kimmel lives now.

After the monologue, on the night he cries with Billy in his arms, the show follows with Jack Black, the ESPN College GameDay guys, a bit with George Clooney, and then, on the outside stage, the band Walk the Moon. For the long day of work, it’s amazing how quickly it all disappears. Jimmy introduces the band to raucous cheers, and as they kick into gear, he re-appears backstage and begins speed-walking back into the building, fist-bumping and high-fiving, bounding up the stairs to the top floor and into his office, where he throws off his suit jacket and tie.

He cried. So what. It was beautiful. And he feels lighter, this long week of Billy’s operation, the recovery, the sleepless hospital nights, the other suffering kids, the monologue, the obligation he felt to talk about Billy and CHIP and those families with little kids who aren’t gonna get the care they need if Congress can’t stop looking at itself in the mirror and vote the damn thing through. Over! He’s said his piece—and a weight has lifted. He can go back to being all funny tomorrow. “It feels like vacation just began,” he says.

I’m reminded of something else Jimmy had said when we were Ubering somewhere. Our driver was a bit of a wild card, the kind who might compel you to say a little prayer if you’re the praying sort, and I asked Jimmy whether he regularly goes to church anymore. He said for him it was all about the sermon, and he hadn’t found anyone inspiring locally. I was wondering why people assume that comedians, digging around in the dark corners of our id, must all be atheists. He agreed, and objected: “I think that’s complete nonsense. If you believe the Bible, Jesus’s friend was a prostitute. I want to imagine that Jesus had a sense of humor. There had to be one disciple that everyone made fun of, you know? Probably Judas. I don’t think making a joke is unholy. I don’t think curse words are against the teachings of the church. When you tell a joke, you’re honoring people, telling them you know them, that you’re paying attention to them and that you have some understanding of who they are. It’s a compliment because you’re noticing them. I bristle at the notion that there’s anything sinful about telling a joke or about certain subject matter. I feel like it’s the opposite of that.”

Now someone brings Billy into the room, and Jimmy takes him in his arms and sits on the couch, holding his hands as Billy squawks. Jimmy keeps looking at him, with almost stunned wonder: “He thinks we understand exactly what he’s saying. He thinks he’s in this conversation.” And then Jimmy laughs, the purest laugh of the day.

The scariest part, Jimmy admitted to Molly afterward, was that before the operation he’d been subconsciously telling himself “Don’t get too attached to this child,” in case something went really wrong. And Molly had admitted to Jimmy that inside she’d felt the same. And then Billy came through.

When Jimmy brought Billy out that night, when he brought him into the stage lights like that, he was also telling the world something about love and perseverance, fear and what it feels like to give your heart away to a kid with a hole in his. How our attachments to one another are forever.

Put it on Jimmy Kimmel’s tombstone: For someone who did nothing but fuck around, he didn’t fuck around.

It was beautiful.

Jimmy Kimmel goes undercover on the Internet and responds to real comments from Twitter, Reddit, Quora, Wikipedia, YouTube, Facebook, IMDB, and more. Why are Jimmy Kimmel and Matt Damon enemies? Is he scared of the ocean? How much of Jimmy Kimmel’s beard is eyebrow pencil?